BODIPY FL L-Cystine

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BODIPY FL L-Cystine

BODIPY FL L-Cystine

Catalog Number F01-0172
Category BODIPY
Molecular Formula C34H38B2F4N6O6S2
Molecular Weight 788.44
Catalog Number Size Price Quantity

Product Introduction

BODIPY FL L-Cystine is a thiol-reactive, green-fluorescent dye. The cystine disulfide is reversibly reactive with various thiol-containing biomolecules, and this compound yields a mixed disulfide fluorescent product. It is relatively insensitive to environment and pH changes.

Chemical Information

Synonyms EverFluor FL L-Cystine
IUPAC Name (2R)-3-[[(2R)-2-carboxy-2-[3-(2,2-difluoro-10,12-dimethyl-1-aza-3-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-3,5,7,9,11-pentaen-4-yl)propanoylamino]ethyl]disulfanyl]-2-[3-(2,2-difluoro-10,12-dimethyl-1-aza-3-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-3,5,7,9,11-pentaen-4-yl)propanoylamino]propanoic acid
Canonical SMILES [B-]1(N2C(=CC(=C2C=C3[N+]1=C(C=C3)CCC(=O)NC(CSSCC(C(=O)O)NC(=O)CCC4=[N+]5[B-](N6C(=CC(=C6C=C5C=C4)C)C)(F)F)C(=O)O)C)C)(F)F
InChI InChI=1S/C34H38B2F4N6O6S2/c1-19-13-21(3)43-29(19)15-25-7-5-23(45(25)35(43,37)38)9-11-31(47)41-27(33(49)50)17-53-54-18-28(34(51)52)42-32(48)12-10-24-6-8-26-16-30-20(2)14-22(4)44(30)36(39,40)46(24)26/h5-8,13-16,27-28H,9-12,17-18H2,1-4H3,(H,41,47)(H,42,48)(H,49,50)(H,51,52)/t27-,28-/m0/s1
InChI Key IUOBNSXKYBKQEY-NSOVKSMOSA-N
Appearance Solid Powder
  • Product Specification
  • Application
Excitation 492
Emission 492

BODIPY FL L-Cystine is a fluorescent dye conjugated to L-cystine, a naturally occurring amino acid. This compound belongs to the BODIPY (boron-dipyrromethene) family, known for its exceptional brightness, photostability, and sharp fluorescence emission. The "FL" designation refers to the specific spectral properties of the dye, which emits in the green wavelength range (around 510-5,50 nm). BODIPY FL L-Cystine is commonly used in various biochemical and biological applications, particularly for studying cystine transport, cellular uptake, and oxidative stress pathways.

One key application of BODIPY FL L-Cystine is in oxidative stress research. L-cystine is an important precursor for the synthesis of glutathione, a key antioxidant in cells. By labeling L-cystine with the BODIPY FL dye, researchers can track its transport and uptake in cells and tissues, providing insights into how cells handle oxidative stress. This is particularly useful in studying diseases associated with oxidative damage, such as neurodegenerative diseases, cardiovascular diseases, and cancer.

Another significant application is in the study of amino acid transport. BODIPY FL L-Cystine can be used to monitor the uptake and efflux of cystine across cellular membranes. This is valuable for understanding the role of cystine in cellular metabolism and its transport mechanisms, which are critical in maintaining cellular redox balance. This application is especially important in research related to amino acid transporter dysfunctions and metabolic disorders.

BODIPY FL L-Cystine is also employed in fluorescence microscopy for visualizing cellular processes. The dye's bright fluorescence allows researchers to observe the distribution and localization of cystine in live cells, offering real-time information on its role in cellular functions. This application is useful in studies involving cell metabolism, protein synthesis, and cellular signaling. Researchers can use BODIPY FL L-Cystine to track cystine within specific organelles or cellular compartments.

Additionally, BODIPY FL L-Cystine is used in drug discovery and screening. The dye allows for high-throughput screening of compounds that modulate cystine transport or influence glutathione synthesis. This can lead to the identification of potential therapeutic agents that target redox homeostasis, offering new avenues for treating diseases linked to oxidative stress. Its fluorescent properties make it an ideal tool for real-time monitoring in drug development.

Computed Properties

Hydrogen Bond Donor Count 4
Hydrogen Bond Acceptor Count 14
Rotatable Bond Count 15
Exact Mass 788.2416483 g/mol
Monoisotopic Mass 788.2416483 g/mol
Topological Polar Surface Area 199Ų
Heavy Atom Count 54
Formal Charge 0
Complexity 1670
Isotope Atom Count 0
Defined Atom Stereocenter Count 2
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes
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